Pros
You'll work with a bunch of really empathetic and kind people dedicated to making the American healthcare system better. Work-life balance is respected, and the company has a mature remote work culture. As an engineer, you'll have no problems getting the tools needed to do your job, and middle management is pretty good at taking care of us and helping us get better at our jobs and advancing. Internal promotions happen often, and you can really grow here as an engineer. Despite any cons, the company is successful, and will be in for an interesting ride over the next few years.
Cons
Life on a product-facing engineering team can be tough. You'll be told your team has areas you're responsible for, but there's a good chance you'll be bouncing around from project to project every few months, with little to no time given to dig into and really own a feature or a domain. And those projects you were told to work on? They're rarely well-scoped, the outcomes are almost never data-driven and the problems rarely well-defined, and by the time you and your team understand what you're doing, it'll be time to slap together something real quick, and move on to the next thing. As a product engineer, you'll have little to no input as to what your team works on, but you'll be held accountable for anything that doesn't go right, even as your stakeholders seem to face no consequences for delivering a barely-baked idea. There also isn't a ton of innovation happening in the product engineering space, and leadership can be resistant to change, even if it brings improvement (or brings the software in line with modern technical standards). Benefits are starting to feel skimpy, especially if you're in a major metro area. The company still has no sick leave, the education benefit is small and hard to use, and HR seems totally out of touch (to the point where they just implemented a new, god-awful PTO and payroll management system with zero feedback from employees). Salary is lower than what you'll make at similarly-sized and "tech-y" companies. Despite a lot of talk, engineering leadership has totally failed to make any real inroads at hiring a more diverse team.